The Reason Tupac Broke Up With Madonna

A new letter from Tupac to his ex-girlfriend, Madonna, has surfaced and made its way to auction. In the letter, the late rapper explained that his decision to call it quits with the pop icon came from mixed feelings related to culture and race. Apparently, it was too hard for him to look past the potential for criticism from some people who might take issue with him dating a white pop star. He wrote:

For you to be seen with a black man wouldn't in any way jeopardize your career, if anything it would make you seem that much more open and exciting. But for me at least in my previous perception I felt due to my 'image' I would be letting down half of the people who made me what I thought I was.

Wow, it sounds like Tupac was torn up about his break-up with Madonna. In fact, the letter helps to underscore the genuine love and deep respect the two stars held for each other. However, societal pressures about culture and race weighed too heavily on the rapper and brought the relationship to an end.

At the beginning of the letter, Tupac wrote about having a hard time finding the right words to say to explain the split. According to the rapper, he did a lot of soul-searching while at the Clinton Correctional Facility where he served time for sexual assault. It brought him to a state of enlightenment where he could sit back and reflect on ways he might have been better. For example, in a line layered with insights about Tupac and Madonna's private conversations, the rap legend wrote,

I must apologize to you because like you said I haven't been the kind of friends I know I am capable of being.

In the letter, which TMZ shared with some parts omitted, Tupac admitted how hurt he felt after they had split up and he heard Madonna joke, "I'm off to rehabilitate all the rappers and basketball players" in an interview. Tupac suggested he lashed out with words at that time because he felt the need to defend himself and protect his ego. However, the rapper's tone in the letter was apologetic.

Now the pop culture artifacts company Gotta Have Rock and Roll is selling the letter at auction. It will be up for sale between July 19 and 28 with a starting bid of $100,000. Another letter Tupac penned in prison sold for $170,000, so experts say this new letter could make a pretty penny.

Back in 2015, during an interview with Howard Stern, Madonna acknowledged her brief but meaningful relationship with Tupac. The Material Girl explained how she and Tupac had been having a heated discourse about the state of the world. The conversation apparently was part of the cause of the infamous David Letterman appearance during which she smoked cigars, used adult language, and appeared incoherent.

The letter is fascinating. It offers such a rare glimpse into the lives of the two music icons. Surely it will be a pricey purchase for whomever bids high enough to get it.